How to Road Trip in the Age of Instagram

For Jack Kerouac, road tripping was all about worlds rich with possibility, people mad to live, and golden lands ahead. It was a romantic adventure fueled by jazz, curiosity, and style. Somewhere along the way, though, the Great American Road Trip lost its cool. What began as an adventure in aesthetics became a slog in baggy T-shirts and flip-flops, fueled not so much by style as by Big Gulps and economy-sized bags of Doritos.

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But now we're living in the Age of Instagram, and while the duck face and food portraiture barrage may be hard to endure, the bright side is that style matters again. No more cutoffs or tie-dyed parachute pants for your drive through Texas just because they're comfortable. Today, traveling is as much about aesthetics as anything. And to help make sure that your next road trip is as Instagram-worthy as possible, we asked photographers Mikael Kennedy and Jace Lumley, plus retail consultant Zach Lynd, three guys known as much for their wanderlust as for their fashion sense, to offer up their tips on how to travel with style.

Keep stylish, even while driving

For some, the temptation might be to go ultra-casual during the drive, and then to slip into something more stylish for the photo-op. But road trips, by their nature, are unpredictable, and you should always be prepared. Jace Lumley, who's worked with fashion brands like Ernest Alexander and A.P.C., learned this lesson while on his recent road trip from New York to L.A. "It took too long to keep changing. Eventually I gave up dressing casually and had on something remotely stylish most of the time," he says. "No one wants to see me in front of the Grand Canyon in Nike gym shorts."

Focus on "pivot" pieces

For Mikael Kennedy, who documented 10 years of wandering through the U.S on his Polaroid travel blog, Passport to Trespass, the trick to traveling stylishly is to focus on the jacket and shoes. "This comes from my hitchhiking days," says Kennedy. "Everything is built around the jacket and shoes." For Zach Lynd, a partner in Kizmet World, a retail and hospitality consultancy, it's all about what he calls pivot pieces. "I always pack pieces that I can 'pivot' from one look to the next—like pants that work for day, but can pivot to evening with an added blazer. Then the next day, you pivot the blazer with something more casual for adventuring." It's about being strategic to get the maximum use out of a few key pieces.

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Courtesy: Baracuta

Mix darkness and light

In order to save space while maximizing versatility, Lumley recommends packing one dark version and one light version of a few key items. A dark T-shirt and a light one, dark denim and a light pair, a dark button-down and a light one, and so on. "It makes it easy to mix and match, whether you're changing in the car or in the hotel room," says Lumley. And if you stick to monochromatics, you'll give yourself the most possible combinations while also taking up the least amount of space.

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Travel light and shop along the way

"Pack your bag, then dump it out and take about half of what's there," recommends Kennedy. "I find I end up wearing the same thing most of the time anyway." For Lynd, traveling light is an attitude. The key is to pack only your best, most trusted pieces, and to always dress for the adventure you want to have. And most importantly, to pick up stuff along the way. "I like to travel with a coterie of great basics, then shop on the road for site-specific additions," he says. "If you know you're going somewhere with great shopping options, roll a military-style, canvas duffle bag up in your suitcase to accommodate all those extra treasures."

Consider a uniform

"I usually just wear a uniform," says Kennedy. "Mostly white tees or button-downs, so it's pretty easy to keep it basic." By sticking to a uniform you can streamline your travel wardrobe without compromising on style. Designer Thom Browne is a great example. He always looks impeccable in his uniform of gray suits, white oxfords, and black ties. But it's also a look that would travel well, even on a long road trip. All you'd need is a spare suit in a garment bag and a weekender full of fresh white shirts. Of course, for those not willing to suit up, a basic uniform of denim and T-shirts, or button-downs, is a great way to keep stylish without having to work too much for it.

Mr Porter; Gitman Vintage

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Be prepared to go formal

"I knew this old photographer who spent most of his time traveling through India, Nepal, and South America," says Kennedy. "He always carried a white shirt in a plastic bag in his backpack, because he never knew when he would be invited to dinner." You probably won't need to break out the tux during your road trip, but that doesn't mean you shouldn't be prepared for a more formal setting. "I don't travel with a full suit, but I'm confident I could put together a formal look," says Lumley. "It would most likely consist of a blazer, a T-shirt, dark denim, and a pair of boots." Again, it's all about the jacket and the shoes.

For a low-mileage trip, drive vintage

"Your choice of car really sets a tone for your journey," says Lynd, who mostly drives vintage cars. "And doing it right means never a dull moment. Plus you'll make friends everywhere you go." He recommends choosing the look of the car based on your destination—like a convertible for California, or an old Jag for the English countryside. And while it may be hard to pull off vintage for a full-on road trip, for lower-mileage adventures, Lynd says that you can find enthusiasts in almost any city who will rent out classic cars out for a few days.

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Getty ImagesRobert Deutschman

Use your trip as a chance to break something in

"I try to buy a new pair of boots if I'm going for a long trip," says Lumley. "By the time you're done, they look two years old and amazing." The road trip break-in is a great way to make anything new look like a well-worn favorite. Boots, suits, raw denim, whatever it is that you want to appear lived-in. "I've always wanted to take a suit out on the road," says Kennedy. "Drive across country wearing it; sleep in it, hitchhike in it, treat it like an old pair of jeans and watch it break in."

Don't cut out the grooming completely

While you can relax your grooming routine somewhat on the road, it's no excuse to go full hobo. Lumley recommends Burt's Bees facial cleansing wipes for a quick freshen up. "Dry shampoo is also a life saver for medium to long hair," he says. "Get over the idea that it's just for girls, and ditch the grease-ball hair." Kennedy is a big fan of a brand called Juniper Ridge for traveling. "Usually I have one of their Backpacker Colognes in my bag, and some of their trail soap." Lynd recommends picking up a new fragrance when you travel. "It's wonderful to pair scent memory with your travel experiences—for the rest of your life, any time you smell it you'll be transported straight back to that adventure."

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D.S. & Durga

And finally, some Instagram advice from the pros

"Stop taking pictures of your food," says Kennedy. "Seriously, no one cares." Beyond that, he recommends thinking of every photograph you take as a self portrait, even the ones you're not in. "It's your perspective that you are presenting to the world, and the summation of them all help paint a picture." For Lumley, it's all about making sure you get the shot, no matter what. "Don't be afraid to get the car messy. It's impossible to keep everything packed when trying to dig through camera gear and clothes. You can repack later, just get the shot while you're on the road."

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